Boston is a historic city with interesting stories to tell, depicted through numerous heritage sites, churches, and old buildings that date back to the 17th century. One of them is the Paul Revere House, built around 1680. It’s currently the oldest structure in downtown Boston, which stands today as a museum open to the public.
Whether it’s an extended holiday or a long weekend, there are so many things you can do to fill in your 3 days in Boston itinerary. Take your family and spend your summer afternoon at the Boston Public Garden and go on a fascinating swan boat ride or take a picture of the famous Make Ways for Ducklings statues.
Perhaps, you want a relaxing stroll along the city’s cobblestone streets or to tour Fenway Park, home of the Boston Red Sox. You can also walk the Freedom Trail and stop by its historic landmarks or step back in time at the Boston Tea Party and Ships Museum. Seriously, you’ll never run out of anything to do during your 3 days in Boston!
The city has reliable public transportation and is easy to navigate on foot, with major attractions relatively close to each other. There’s also an abundance of restaurants, activities, and entertainment options to ensure your 3 days in Boston are packed with fun and adventures from sunrise to sunset. So gather your unneeded items and store them at Bounce luggage locker to make the most of your trip. Don't let anything slow you down!
Boston itinerary - Day 1
Morning: Hike at the Freedom Trail
There’s probably no better way to start your 3 days in Boston than walking the Freedom Trail. This iconic trail is distinguished by the 2.5-mile red brick path through sixteen nationally and historically significant sites and monuments. These include churches, meeting houses, battlegrounds, and areas that played a crucial role during the Revolutionary War.
The walking tour starts at Boston Common at 139 Tremont Street in Downtown Boston. It was established in 1634, making it the country’s oldest city park. You can find the Visitor Information Center at the park to get the brochure with information on each site. Then it will take you to the Massachusetts State House, which has served as the Massachusetts government’s seat since it opened in 1798.
From the State House, the trail will lead you to Park Street Church, featuring lofty architecture and the 217-feet steeple. It used to be the first landmark visitors saw when approaching the city. It will continue through Granary Burying Ground, the King’s Chapel & Burying Ground, Benjamin Franklin Statue/Boston Latin School, the Old Corner Bookstore, the Old South Meeting House, and the Old State House.
The Boston Massacre Site is also one of the stops you should take the time to explore. A deadly riot occurred at this site on March 5, 1770, killing five men and wounding others. Other attractions and historical markers you’ll see along the way are the Faneuil Hall, Paul Revere House, Old North Church, and the Copp’s Hill Burying Ground. At the end of the trail is the USS Constitution Museum, offering interactive exhibitions, two historic shops, and engaging programs for students, adults, and families.
Your final stop is at the Bunker Hill Monument in Charlestown. It was built between 1824 and 1843, but the 221-foot granite obelisk was completed in 1842. Just across from the monument, you can also stop by the Ball of Bunker Hill Museum. It houses artifacts from the battle, including a sword, a snare drum, and a masonic apron that belonged to Dr. Joseph Warren, a revolutionary leader who died in the fight.
You can schedule a guided walking tour, which takes around 90 minutes. But if you want to explore on your own and at your own pace, you can go for a self-guided tour. Note that some sites offer free admission while others require tickets to enter.
Afternoon: Lunch and Visit to The New England Aquarium
You deserve a hearty meal after nearly three miles of a historical journey through the Freedom Trail. So before heading to your next destination, refuel at Warren Tavern, located on the charming streets of Charlestown. It is one of America’s most historic taverns and the oldest in Massachusetts. It has served many prominent individuals, including Paul Revere and George Washington. Its comprehensive menu includes burgers, sandwiches, salads, and wraps.
After lunch, the next stop on your Boston itinerary is the New England Aquarium. With over a million visitors each year, the Aquarium is one of the city’s main attractions, giving everyone extraordinary learning and learning experiences. It offers an array of exciting exhibitions, including the East Coast’s largest shark and ray touch tank, the Giant Ocean Tank, and hundreds of Caribbean animals. You can also see two giant Pacific octopuses and diverse, colorful marine creatures from the Pacific Northwest at the Olympic Coast exhibit.
Night: View at Skywalk Observatory
If you’re visiting Boston for the first time, one of the top attractions you should include in your Boston itinerary is the Skywalk Observatory. Even Bostonians recommend making it your first stop, so don’t let the day end without seeing the city from the Observatory. It is open until 8 pm, but if you come before the sun sets, you can see up to a hundred miles away on a clear day.
The Observatory is the second tallest building in Boston at 729 feet, allowing visitors to enjoy 360-degree views from around 700 feet above the ground. You’ll get a bird’s eye view of Fenway Park, the Charles River, the Charles River Esplanade, the Boston Common, Boston public gardens, Harvard University, MIT, and countless other city landmarks. Plus, it has a movie theater and offers interactive and enriching exhibits that show the city’s cultural history.
Boston itinerary – Day 2
Morning: Fun at Boston Public Garden
Right next to the Boston Common is the Boston Public Garden, the country’s first public botanical garden established in 1837. It has been flowery and decorative since its inception, with fountains, statues, plants, flowers, and trees bringing life and color to the Garden. Surrounding the Garden is a Victorian cast-iron fence and meandering pathways perfect for a morning stroll.
One of the remarkable features of this Victorian-era garden is the 4-acre lagoon where you can ride on the famous Swan Boats. The Swan Boats have been in operation for more than 100 years and are among the favorite attractions in Boston Public Garden. Due to the Garden’s ethereal beauty, romantic setting, and wide variety of gorgeous flowers and plants, it attracts numerous couples who want to hold a garden wedding.
Afternoon: Time at the Seaport District
Across from Downtown Boston is a vibrant neighborhood on the south end of Boston Harbor. The Seaport District is a great place to explore on a warm or cool afternoon, packed with numerous shops, boutiques, and eclectic waterfront restaurants, delivering extraordinary dining opportunities. Whether it’s casual or high-end luxury dining, the Seaport District's lively dining scene won’t disappoint you. You can also walk along the waterfront, stop by one of its cafes for a quick bite, or shop for some unique gifts and treasured souvenirs.
Also found in the Seaport District are several concert venues, museums, and other cultural facilities. These include the Institute of Contemporary Art, the Boston Tea Party and Ships Museum, the Boston Fire Museum, and the Boston Children’s Museum. It’s also home to the Blue Hills Bank Pavilion, one of Boston’s premier amphitheaters, which has hosted some of the most memorable concerts and events in the city.
Night: Cruises and Tours
Your trip to the city won’t be complete without going on one of the iconic Boston harbor cruises. See Boston Harbor at its best as the sun sets and the magnificent building lights turn on, creating a magical view you won’t forget. You can enjoy dinner as you take in the views of the city skyline from the water. It can be dark for a whale-watching tour, but if you head out into open water before the sun sets, you might spot one or two of the most majestic oceanic mammals in the area.
Try the Boston Duck Tours, which lends sea and land perspectives to the city’s history and architecture. It offers a revamped WWII-era vehicle that will take you to areas where you can see the Cambridge and Boston skylines. If you want to combine a delicious dinner with a relaxing cruise and some sightseeing, consider Odyssey Cruises. They provide freshly-prepared meals for guests and take you to some famous landmarks around.
Boston itinerary - Day 3
Morning: Try a Fenway Park Tour
Whether you’re a baseball fan or not, never miss the phenomenal Fenway Park tour on your final day in Boston. Opened in April 1912, Fenway Park is the oldest and one of the legendary ballparks in the United States. It was also touted as “America’s Most Beloved Ballpark” due to the exciting and enthusiastic atmosphere outside the stadium you can’t experience anywhere else. Every time there’s a game, the streets outside are closed before the game so people can enjoy great food, live music, and mingle with other fans.
The ballpark is home to the Boston Red Sox, who played their first game here against the Yankees on April 20, 1912, and drew around 27,000 spectators. But one of its notable features is the 37.2-foot green wall in the left part of the field called the Green Monster. The tours are available year-round between 9 am to 5 pm. During game days, the last tour leaves three hours before game time.
Afternoon: See the Museum of Fine Arts and Isabella Stewart Gardner Museum
Just a show walk from the ballpark are two magnificent museums, the Museum of Fine Arts and Isabella Stewart Gardner Museum. The Boston Museum of Fine Arts is one of the country’s leading art museums, with an outstanding collection of ancient Egyptian treasures, European paintings, Asian fine arts, British Art, and more. It has over 100 galleries open to the public and offers virtual tours, music instrument demonstrations, lectures, and curator talks.
The museum’s art collections will give new perspectives as it connects the art of the past and the presented day. Every media type is represented here, including painting, photography, sculpture, decorative arts, film, video, performances, works on paper, craft, and installation.
After touring the Museum of Fine Arts, head to the next cultural attraction in the area, the Isabella Stewart Gardner Museum. The building is an integration of different elements from the Roman, Gothic, Byzantine, and Renaissance eras, creating a stunning, harmonious experience. It contains Isabella Stewart Gardner’s collection of over 75,000 sculptures, paintings, manuscripts, tapestries, decorative arts, and rare books.
Night: Enjoy Dinner and Shopping
No Boston itinerary is complete without setting aside time for shopping and enjoying its booming dining scene. If you’re looking for satisfying retail therapy, go to Newbury Street, located in the historic Back Bay area. Some call it the Rodeo Drive of the East due to the numerous top designer brands you can find here, as well as fine art galleries, boutiques, and unique shops.
Copley Place is another distinctive shopping destination worth exploring in Boston with fabulous and high-end stores. These include Louis Vuitton, Gucci, Moncler, David Yurman, Christian Louboutin, Tiffany & Co., Burberry, and more. You can also head to Prudential Center, home to an array of restaurants offering luxury and casual dining experiences. Located here is the Skywalk Observatory you can always revisit, or discover the different dining, shopping, and attractions around the area.
3 Days in Boston
Maximize your brief vacation and consider this Boston itinerary, consisting of different activities and must-see attractions in the city. It may seem a bit tricky to fit everything you want to do if you only have 3 days in Boston, but with some planning and organization, it’s far from impossible.
You can visit Boston anytime and explore its spectacular sights and attractions on foot through free walking tours or by boat by choosing one of the magical harbor tours and cruises.
Still planning your visit to Boston? Check out these guides for more ideas!